


Upstead One Shot & Drabbles Collection

by whereyougo



Category: Chicago PD (TV)
Genre: Drabble Collection, Drabbles, F/M, Falling In Love, Feelings, One Shot Collection, Partners to Lovers, Snippets, Upstead, one shots
Language: English
Status: In-Progress
Published: 2021-01-10
Updated: 2021-01-10
Packaged: 2021-03-12 22:08:02
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 3,352
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28642704
Author URL: https://archiveofourown.org/users/whereyougo/pseuds/whereyougo
Summary: Here is where I'll be posting many of my one shots and short drabbles for Upstead. All are inspired by scenes I wish existed.
Relationships: Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton
Kudos: 40





	1. Follow You

**Author's Note:**

> These will all be in the CPD Universe and are all inspired by what I wished would have happened in the episodes. As much as I love Jay and Hailey and all the crumbs they've dropped over the years, I need more! 
> 
> The first five drabbles have been moved over from my ff.net account, in case you've read them and they look familiar. I'm slowly moving those works over to here.

**Summary for the Chapter:**

> "Um, I have an assignment." She pauses. "It's in New York."
> 
> "I'm going with you." He blurts out.
> 
> She shakes her head, even though she should know by now that he would react this way. "You're not. This isn't-"
> 
> "No," he's quick to interrupt her, "when I told you I'd follow you anywhere Hailey, I meant it. I looked right at you because I wanted you to know that I've got your back no matter what. No matter where we are; we're together in this. Always."

_Follow You_

She stops and stares into the window of the bar, looking straight at the familiar back she's could spot in any crowd.

As much as she wanted to tell Jay when they were still at the station together, she wanted to take a second and push down the fact that Voight had reminded her briefly of her father. When her sergeant had gotten in her face and screamed at her, something in her had immediate switched to keep herself from breaking. She had to remain stoic to protect herself in this situation because she made herself a promise that she wouldn't let that man break her.

Even though she doesn't like the fact she has to leave, she knows that Voight is doing this for her own good. She can be angry at him all she wants to but she does want to find her place within the unit again.

When Hailey starts to walk over to him, Jay turns as if he could sense that she was in the room. Their bond definitely gives off the vibe that they can still detect each other without even having to be around each other physically.

"Hey," Jay greets her, "I noticed you stayed back after we were dismissed."

"Yeah. Voight wanted to talk to me in his office."

Jay nods. "Is everything okay? I'm asking because you seem a bit off and you know we can tell when the other is lying."

Hailey's teeth skim over her lip. There is no way that she could lie to Jay about this. He's going to find out one way or another. It's going to be extremely obvious that she's not there. She wants to be the one to tell him, after all Jay is her partner and she wants to be the only one he hears things about her from.

"Um, I have an assignment." She pauses. "It's in New York."

"I'm going with you." He blurts out.

She shakes her head, even though she should know by now that he would react this way. "You're not. This isn't-"

"No," he's quick to interrupt her, "when I told you I'd follow you anywhere Hailey, I meant it. I looked right at you because I wanted you to know that I've got your back no matter what. No matter where we are; we're together in this. Always." He's practically pleading with her.

Hailey knows that Jay meant every word he's ever told her. Hailey's told Jay plenty of things too - that she's trusted him since they first met and that she's go with him wherever he went. She's never had a partner like Jay Halstead. There's never been a man in her life that has been someone she can fully rely on. There's no one that's ever protected her in the way Jay has. Hailey's built up many walls over the years and she's never let them down for anyone before Jay - and most likely will never let anyone else in after him.

"So what? You're going to go back home, pack a bag, and go with me to New York?" She asks him, slightly shaking her head. As much as she'd love to have Jay by her side, she knows this is only going to be something Voight thinks will help her. Jay is still needed in Chicago. There's no reason for him to follow her to New York because he wouldn't be any use. Hailey doesn't want Jay to feel like he's useless because he's the exact opposite.

He means so much to the city of Chicago, to the rest of their unit, and so much to her - more than he even knows.

Jay doesn't respond. His eyes briefly drift down to the floor before looking back to her. He swallows back. "I don't like this. It doesn't make any sense. Why is Voight assigning you to New York?"

Hailey lets out a sigh. "I don't like it either but it's a non-negotiable situation."

She can't bring herself to tell him why. She doesn't want to descend into a darkness that she can't free herself from. She can't make Jay be the one to pull her out of it and she knows Jay would do whatever he could to bring her back. She'd do the exact same thing if their roles were reversed. Hell, she's done it a few times already and has felt the fear and pain of thinking that he was dead. She doesn't want him to ever feel that fear and pain about her.

They let each other drag the other through Hell and let each other learn of all of their demons along the way.

"I'm really going to miss you. I feel like we've only just got back to where we were before I was shot."

It still hurts Hailey to hear, even though he's standing right in front other perfectly healthy. She hadn't been there to protect him like she should have been and being left in the waiting room with the thought of having Will tell her that he didn't make it would feel like she was shot too, right in her chest. When Jay pulled through, Hailey wanted to tell Jay that she was in love with him and she didn't want to lose the chance to say it before it was too late.

But she still hasn't been able to tell him and she knows telling him right before she heads off to New York isn't the right time to be confessing her every thought and feeling she's only just begun processing.

Instead, she keeps to their narrative.

"We always fall right back and it'll be just like that after all of this is over. We can't act like this is the end, okay?" Hailey gives him a look, waiting for him to agree with her.

"I'm going to miss you too. It's only for a few weeks, Jay. I'll be back before you know it. I'm not leaving you." She offers him a small smile, trying to reassure him that nothing could really keep her away from him.

"Now I have to go home, pack up, and break the news to Rojas." She crosses her arms over her chest and shakes her head. "Do you think you can check in on her for me while I'm gone? It's tough on her right now and I just want to make sure she can come out of this on the other side."

Jay nods. "Of course. She's going to be all right. She's a tough one. Just like her mentor." He lets out a chuckle and Hailey rolls her eyes at him.

He is right about Vanessa's strength. So far, they've all been impressed with the way their newest teammate has adapted within the group. She can take down men larger than she is and make it look effortless. Hailey knows Vanessa Rojas is meant for Intelligence, and with time Vanessa will know it too.

Vanessa also is the only one who knows her true feelings about Jay. It's not something Hailey's use to talking about yet but Vanessa seems to know Hailey's feeling more than she does. Showing her emotions is one of her toughest battles and being vulnerable is a place she doesn't let herself go to that often. Hailey's never had many girl friends but the women in her squad feel more like sisters to her at this point. At first, she had no clue if she'd fit in with them but luckily it hadn't been too rough of start.

"Thank you, Jay."

He nods again and Hailey can see that his eyes want to tell her more but he's not allowing himself to go there. For right now, it's for the best.

"Don't go too crazy without me." She tries to joke with him.

Jay pulls Hailey in for a hug, his broad body shielding hers and protecting her like it always does. "I can't promise anything. The girl that keeps me grounded is running off on me."

She pulls herself away from the hug and feels as the warmth from Jay's body begins to leave hers. Hailey smiles at him again and lets her eyes linger on him. Soon she won't be able to look to him for the comfort and safety he brings to her each day. The next time she'll lay her eyes on Jay Halstead will be when she returns to him, when she returns home. His blue eyes will be the first thing she looks for. His arms will be the only ones she'll be running to.


	2. Here Without You

**Summary for the Chapter:**

> Looking to her is always a quick reflex. When he looks to her he gets the validation that they're in this together, that they'll always be good. Because they are good and when she returns to them - to him - they'll fall right back into their place; just as natural as a reflex.
> 
> Sequel Drabble to "Follow You"

_Here Without You _

"You look rough." Vanessa Rojas comments as she walks past Jay on her way to deliver a file to Voight. She's been doing her best to keep busy on their latest case since the previous one had been personal for her.

He knows exactly the draining emotional toll personal cases can take. His mind usually goes on overdrive during those times, which says a lot because his brain always seems to be working at an accelerated level when their deep diving into cases.

Jay offers her a short-lived smile. He lets out a sigh as he stares at the desk across from his. Everything else in the room goes out of focus.

He swallows as he lets himself get lost in the times where they would sit next to each other on the end of either one of their desks. He doesn't even know the exact moment where it became their thing. There were times where he almost let himself get lost in the fact that they were almost touching from ho close they sat together. He would hope that if one of them moved that they'd accidentally brush against the other. He thought about doing it on purpose and laughing it off as another way to let Hailey know that he's there. His thoughts would be funny to anyone on the outside but to him they're everything.

It doesn't feel real to him. Even though it's a temporary thing, he also knows that not having her by his side for any amount of time is an eternity. She's been the one next to him for so long, and not just as her job as his partner. She's pulled him out from his own darkness multiple times. Hailey's gone through her own turmoil because of Jay's instinct to risk everything. It's Hailey who saves Jay, not just from the criminals but from himself as well.

Hailey keeps him grounded. When he thinks he has it all figured out, Hailey's suddenly there and checking in on him.

Who is going to be the one he can look to with the same amount of unwavering trust while his partner is away?

That is never a question he even has to ask because Hailey Upton is irreplaceable to him.

He's not saying that he doesn't have trust with the others on the team. Everyone up there with him is considered family to him and he'll always trust and protect them. Hailey's just different. She's on her own level.

Looking to her is always a quick reflex. When he looks to her he gets the validation that they're in this together, that they'll always be good. Because they are good and when she returns to them - to him - they'll fall right back into their place; just as natural as a reflex.

When Voight gave them their assignments this morning, it all felt so off. It wasn't 'Hailey and Jay' or 'Jay and Hailey'. It was Jay and Kim, who had to snap him out of his 'missing Hailey' daze to make him realize he was supposed to be going with her. As he left with Kim, Jay's eyes wandered behind him where he knew Hailey should be.

It's also Kim who can tell that something is off with Jay when they're in the car together, waiting for their suspect to make a move. She didn't make Jay say anything about it but she did let him know she was there if he wanted to talk to her.

Not to ignore what was on his mind, but because he didn't spend much one-on-one time with Kim, Jay let her know that she could talk to him if she wanted to. Kim was going through a major loss and Jay wanted her to know that he's there for her too.

Jay and Kim had each other's backs but not in the same way Jay and Hailey do.

It's not that it takes her being gone for him to think about her this much. Jay thinks about Hailey pretty much all the time. Thinking about her is just the same as breathing for him.

He turns in his chair when he hears footsteps.

"A little bit of advice, why are you getting yourself so down about Hailey? We all know she's kicking ass in New York." Vanessa is back from talking with Voight.

Of course he's knows that Hailey's holding her own with the FBI unit Voight assigned her to. He expects nothing less from her. He still doesn't know what the reason for this sudden change is but he also knows that Voight always has his reasons for his decisions and he always looks out for the members of his unit.

When Hailey told him about her going to New York, Jay was ready to go straight to their sergeant and argue his case for getting him to change his mind. Hailey is his partner and he just got her back. He isn't going to lose her without knowing why he was in the first place.

"Hey, Hailey asked me to check in with you." He says to her as he lamely puts his hands into the pockets of his jacket. When it comes to changing the subject from Hailey, Jay's not very smooth about it.

He gives her a quick glance. "So, how are you holding up?"

"The best way that I can, I guess. Hailey's been a huge help and I've got all of you guys to lean on. As much as I want to say I'm over it, I can't yet. There's still times where I find myself thinking about what I could have done or shouldn't have done to make the outcome different. I tell myself that I'm a cop and there's no reason to dwell on a case closed. It could have been worse but this is it. Time to move onto the next one." She offers him a soft smile. "I'll figure myself out and learn from it."

She steps back from him with a confident nod before walking away from Jay.

Before she reaches the stairs she turns back to him. "Since you're going to be reporting back to Hailey on how we're coping, then you should tell her you're miserable and hopelessly in love with her." Vanessa sends him a sly smile and then lifts her brow before she heads towards the stairs to leave the station.

Jay doesn't go out after her. He's hit with a stillness at her words. Is he that obvious?

Then Jay remembers when he was finally being discharged from Med, and there was something that Hailey wanted to tell him before his phone rang. They're supposed to pick up that conversation that they didn't get to in the hospital. He doesn't know why it hasn't come up since then. If it was important to Hailey, then wouldn't she have brought it up? Or was he supposed to be the one to acknowledge it?

The way she looked at him had forced that same stillness to him. In that moment, he could feel her vulnerability and Hailey doesn't show just anybody that depth. In that moment, she had all of his attention and his heart. He felt like he knew what she was going to say and his broken heart had opened up for her. He never thought he'd be ready to hear those words again but Hailey is the only person he ever wants to hear them from.

All of his emotions had surfaced when she her expression mirrored his own. The way he looked at Hailey was a in a way he's never looked at a girl he loved before. Not even Erin, who hasn't even crossed his mind since she had also gone off to New York.

But his story is no longer about Erin.

It's about the relationship that he's only been able to build with Hailey.

It's about what's going to happen when Hailey returns home to him.

It's going to start the next time he has Hailey wrapped up in his arms. She'll never be going anywhere without him again because he's not going to let her go.

Letting go of Hailey is something that Jay can't even fathom. Letting go of Hailey means he's letting go of the happiness he hasn't felt in such a long time. It's because of her that he wakes up every morning and actually looks forward to the day. He looks forward to spending his time working with Hailey, and sometimes spending a night recap with Hailey - where they don't have to talk but they have each other if they wanted to. There's beer too but Jay prefers Hailey over having a cold one.

Talking to her is one of Jay's favorite things to do. They lay their lives out for each other in the field and they lay out their lives to each other when it's just them.

Their relationship hit a standstill when Jay found out that Hailey was sleeping with Adam. He's never quite understood why Hailey started things up with Adam and he didn't really want to know. Those two together never made any sense to him. He was jealous and he didn't want Hailey to know that he was because then she might know that Jay had feelings for her. She spent more time with Adam than with Jay, which is something he never thought Hailey would do. He didn't want Hailey to have conversations with Adam in the same way she has them with him. Her stories are sacred to him and he hopes his are to her too. Plus, seeing them together hurt. He was sure Hailey didn't want to start a relationship with someone that she worked with - and Jay never thought he'd ever fall in love with another one of his partners either, but he did and, maybe, he's fallen harder for Hailey than he did the first time around.

Just as he hoped, Hailey ended things with Adam, and they were back to being Jay and Hailey.

Except for the fact that Jay still kept his feelings towards Hailey to himself.

Back to his most recent gunshot wound, he could have died and Hailey would never know how he felt about her.

He's done wasting time and skipping around the subject. Jay is in love with her and he knows she loves him too. It's not just about being partners and being good in that aspect. It's about every little thing that they learned about each other and how much they wanted to be wherever the other was. It was about how she admitted to trusting him the day they met and that he could finally breathe easily again knowing that Hailey was in his life.

Instead of dreading each passing second without her, Jay is going to look forward to each second passing by until she's back and each new second he gets to be with her.

Vanessa is still outside, as if she's been waiting for him to follow her. Another smug smile graces her lips as she crosses her arms over her chest. "Ask me. I know you want to." She challenges him.

"Did Hailey ask you to check on me too?" He can easily guess that she would because when Hailey cares about someone, she never stops making sure that they're okay.

She playfully shrugs before patting Jay on his shoulder. "Of course she did. You're her partner." She winks to him.


End file.
